Lecture 12a Proposal

Introduction Goals Research information in the literature using Scifinder, Reaxys, etc. that helps to propose a pathway to the synthesis of a compound assigned to you and your partner by the instructor Propose detailed procedures (which substitutes for your pre-lab minus the safety data) to be followed in the lab based on the work that was previously been performed in the field Propose spectral data and physical properties based on published data Apply the lab techniques introduced in Chem 30XL courses Learn on how to work efficiently in a team (for most parts) Writing a proposal Giving an oral presentation

Structure of the Proposal I Abstract It briefly states the desired goal of the project (1-2 sentences) Introduction It shows that the students performed literature search and evaluated different procedures for their feasibility to be carried out in Chem 30CL One alternate procedure for each step has to be shown and briefly discussed Discussion It discusses the basic idea of the synthetic approach chosen for the lab It shows the key step of the mechanism of the reaction as carried out in the lab

Structure of the Proposal II Experimental The exact amounts of reactants used (g and mol) The exact amounts of solvent (mL) The exact reaction conditions (temperature, time, etc.) A detailed account on how to monitor the progress of the reaction i.e., TLC (mobile phase, etc.) Expected observations i.e., color change, evolution of gas, precipitation, etc. A detailed account of the workup/isolation of the crude product Purification steps Recrystallization: solvent or solvent mixture (including the proposed ratio) Flash chromatography: mobile and stationary phase

Structure of the Proposal III Characterization Melting point Infrared spectroscopy UV-Vis spectroscopy 1 H-NMR spectroscopy 13 C-NMR spectroscopy Mass spectrometry Note that the melting point cannot easily be extrapolated from other compounds because minor changes in the structure can have a significant impact on the way the molecules arrange in the crystal If the exact compound cannot be found, a very similar compound should be used as reference and the expected differences be rationalized in the infrared, NMR and UV-Vis spectrum of the compound because trends can be predicted in this type of data Spectra that have been simulated with Chemdraw, ACD software or Spartan are not acceptable here. Note that these programs cannot account properly for the ferrocene part.

Structure of the Proposal IV Reference section Follow the same guidelines like the report A copy of the key references (synthesis and spectroscopy) have to be attached to the proposal, properly labeled (numbered) and organized Simulated spectra ≠ literature spectra

Limitations in the Lab Note that there many limitations to the work performed in Chem 30CL Time: four meetings with 3-4 hours each, this means that no overnight reactions are allowed, particularly those requiring reflux Hazards: chemicals that are very difficult to handle or are dangerous will not be provided in Chem 30 CL i.e., BuLi, LDA, LiAlH 4, NaH, DMSO, chlorinated solvents, very dry solvents, etc. Techniques: the lab is not able to provide a setup for strict inert gas techniques (Schlenk techniques), however basic inert gas technique i.e., nitrogen balloon is doable Cost: expensive catalysts i.e., Pd-based, etc. are not available

Chemicals and Equipment The following chemicals are usually provided Substituted benzaldehydes (X=Hal, OR, NO 2, Alkyl, etc.) Phenylhydrazine Trimethylsulfoxonium iodide ([Me 3 S(=O)] + I - ) Standard solvents i.e., hexane, ethanol, methanol, ethyl acetate, THF, diethyl ether, etc. Compounds like potassium hydroxide, glacial acetic acid, Aliquat 336, etc. A microwave will be provided as well. If you plan to use it, make sure to get trained on it first by your TA.

Other Considerations The proposal should only be six (6!) pages long Both group members have an obligation to contribute to the proposal (and the in-lab work) equally which means that they will receive the same grade for the proposal The proposal has to be submitted in a proper report folder like the Jacobsen paper, possess a proper title and the name and addresses of the students on the front page The proposal has to be submitted in a proper folder to the instructor by November 21, 2014 at 4:30 pm The proposal (one per group) has to be submitted to by November 21, 2014 at 5 pm as well. Failure to do so will result in an automatic 5-point deduction The experimental work for the project will be conducted from December 2, 2014 to December 5, The students generally will only be allowed to attend their own lab meeting! The oral presentation showing the results will take place on December 9, 2014 in YH You and your partner have to sign up for it in the instructor’s office asap.